Potassium Carbonate → 4-(2-Fluoro-4-nitrophenyl)-1lambda~6~,4-thiazinane-1,1-dione

HRID 56097Notes

Reaction equation

HRID 56097 reaction equation
C([O-])([O-])=O.[K+].[K+].Cl.[O:8]=[S:9]1(=[O:15])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[F:16][C:17]1[CH:18]=[C:19]([N+:24]([O-:26])=[O:25])[CH:20]=[CH:21][C:22]=1F>CS(C)=O.O>[F:16][C:17]1[CH:18]=[C:19]([N+:24]([O-:26])=[O:25])[CH:20]=[CH:21][C:22]=1[N:12]1[CH2:13][CH2:14][S:9](=[O:15])(=[O:8])[CH2:10][CH2:11]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 12324096Thiomorpholine 1,1-dioxide hydrochloride

Product 1

HCID 159843694-(2-Fluoro-4-nitrophenyl)-1lambda~6~,4-thiazinane-1,1-dioneYield 110.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of K2CO3 (5.53 g, 40 mmol) and 1,1-dioxo-thio-morpholinehydrochloride (3.60 g, 21 mmol) in DMSO (50 mL) was added 3,4-difluoronitrobenzene (3.18 g, 20 mmol). The reaction was heated at 100° C. for 12 h. The mixture was diluted with water (150 mL) and extracted with CH2Cl2 (100 mL×2). The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo to give the title compound as a yellow solid (6.04 g, 70%).

Workup

  1. extractionextracted with CH2Cl2 (100 mL×2)
  2. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-99e1f1d0b8b147e5b818e5bd1574fa0a
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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